Chai Mai Jing Ying Tae

Rin is an office girl who is suddenly unemployed. She has many problems, such as paying off her condo, telephone, car and other expenses. While her life is hard, Rin meets Ken, a nice middle-aged man. Ken has experience with cabarets and beauty contests of transgenders. He's also unemployed and in need of money, so he tells Rin about the price money and makes her enter a beauty contest prentending to be a transgender. Rin feels bad about lying to people, but she wins the contest and becomes popular. As the winner, she's invited to play the lead role in a lakorn directed by Pao, a famous director who falls in love with Rin. But he's confused about his feelings and he must choose between following his heart or his social position, because his family can't accept a transgender woman.
(Source: MyDramaList)